Divorce Support Forums: My boss? Advice please.

Here's the thing. He's a whole different generation from you. I'm guessing he's closer to my age. Men of my age group do not take sex as lightly as I gather men of your age group do. And FWB may sound fun to them in a real mid-life crisis kind of way, the same way that they always look a little more interested whenever a woman suggests she may be bisexual and he starts imagining the possibilities of having a 3-way... for MY generation, they really are considered nasty types if they do more than just imagine & joke about it!

Not that he would necessarily fall in love with you... more likely quite the opposite, he'd start to disrespect you TREMENDOUSLY.

Now, I worked in an industry where a significant portion of the support staff believed that they were entitled to pursue relationships with the professional staff and if they could make it work then they'd snagged themselves a great guy. The ones who were doing it believed EVERYONE was doing it, and the ones who were not were always appalled about it. THe ones who WERE usually could point to friends who had done it and not bothered their careers... but I was on the professional staff side of this and watching lots of my men friends treating various assistants like thier own personal little dating service... and I can tell you that careers were ruined.

There was never one of these that started where they thought it would progress fartehr than FWB (at least on the guy's side) but about half of them would end up with something wrong happening. I watched one friend stalk his former clerk. Another lost his job because several of his former lovers (FWBs if you want to say that) found out about each other & got angry. I saw clerks & assistants shifted from assignment to assignment as thier career paths fizzled because no one wanted them in their devision because they had that kind of reputation that would cause everyone to nudge each other & wink if the boss was even a tiny bit of a possible fwb for her.

Yet several clerks... their whole purpose fo rentering jobs in our office was the possibility of finding a great guy with a great job to hook up with and they truly believed like you did... that it did not matter.

From the perspective yuo're looking at, nothing bad can happen, and if it does, you can always sue. But why set yourself up for it? Why set him up for it?

Once sex enters into the picture, I don't care how casually you take it... people's emotions change.

At the very least, you'll know intimate things about each other that employers & employees should not know about each other. His next girlfriend after you might just be THE one... the one he flips for and wants to marry, and guess where you'll be THEN... certainly not anyplace where there is a danger that his new sweet wife-to-be might EVER have a private talk with you where she would find out any intimate details... not that you'd betray the trust, but he'd be a fool to trust anyone with the private information around the woman he loves.

This is about as ill-advised as one of those kids who tapes themselves doing the deed and then tosses it onto a computer & maybe thier myspace just for fun. I guess it's a generational thing, but I would NEVER have considered that any more than I'd consider a fling with a boss.

I can tell you that from my perspective... probably about 20 years further along in life than you... the people who have succeeded in life are NOT the ones who took sex that casually... and I am from a generation where free sex was truly a possibility because we had just been given access to reliable birth control and the worst STD you could get was herpes. Married people were doing Key parties and our brothers & sisters were moving to communes where free love was not associated with a very strict and cloistered religion. We were not so uptight as it might sound... but we didn't have access to the internet for use in ruining our reputations for life... and we didn't have situations like the Clarence Thomas confirmation hearings to look at as possible problems to our careers if we made an off color remark. We were naive and free and we truly did not have any reason to believe that anything we did would follow us forever...

So some people DID do exactly what you're planning. THey DID participate in wife swapping, they did try to sleep thier way up the corporate ladder. They looked for Mr. Goodbar or had casual sex with friends & strangers without any feelings of moral guilt or outrage.

NOW, 20 -30 years later... if they did it back then, they are embarassed about it and don't really want anyone talking about it... Or they are not particularly successful in the long range with careers or relationships.

But do what you want. You seem headed towards it anywyas. Youve thought through all the excuses for why it's right and OK to do... just like the kids who put embarassing stuff about themselves on YouTube... go for it. I just hope you don't find yourself embarassed, demoted, transferred, uncomfortable at work, etc., etc., etc.